Ethyl Acetate → HCID 67463851, compound

HRID 1845904Notes

Reaction equation

HRID 1845904 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])C(OC)=O.[CH3:13][Mg]Br.C([O:19][CH2:20][CH3:21])(=O)C>C1COCC1.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([C:20]([OH:19])([CH3:21])[CH3:13])[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 7015747Methyl 3-bromo-4-methylbenzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 67463851HCID 67463851, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of methyl 3-bromo-4-methylbenzoate (25 g, 110 mmol) in THF (110 mL) at −78° C. under nitrogen was added methylmagnesium bromide (85 mL, 250 mmol, 3M in THF) slowly and allowed to stir for 30 minutes. The reaction was warmed to room temperature for 30 minutes and the solution was diluted with ethyl acetate and sodium bicarbonate. The solution was then extracted with ethyl acetate, washed the combined organic layers with brine, dried over sodium sulfate, filtered and concentrated to afford 2-(3-bromo-4-methylphenyl)propan-2-ol (2-1) as a white solid.

Workup

  1. extractionThe solution was then extracted with ethyl acetate
  2. washwashed the combined organic layers with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d21a9835f3174382af7901cd9ae25cdc
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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